Dibutyltin bis(2, 4-dinitro-6-alkylphenolates)



3,409,653 Patented Nov. 5, 1968 United States Patent Oflice 3,409,653 DIBUTYLTIN BI 2,4-nrNr TRo-6-ALKYL- PHENOLA Walter A. Stamm, Tarrytown, N.Y., assignor to Staulfer Chemical Company, New York,

N.Y., a corporation of Delaware at least one of the para and ortho This application is a continuation-in-part of US. Ser. No. 286,521 filed June 10, 1963, and now abandoned.

This invention relates to organotin compounds. 'Inpar ticular, the invention pertains to ortho-substituted dial-kyltin bis-nitrophenolates and the method of preparing them.

The dialkyltin bis-phenolates constitute a class of orhandicapped because of their instability.

It is, therefore, the primary object of this invention to provide a class of dialkyltin bis-phenolates which are proneness toward moisture purposes will become apparent subsequently herein.

can be conveniently depicted by the following general formula:

wherein R is alkyl of from I to 12 carbon atoms, e.g., methyl, ethyl, n-propyl, isobutyl, n-butyl, n-pentyl,- nhexyl, n-heptyl, n-octyl, isooctyl, n-nonyl, n-decyl, n-dodecyl, and the like; X represents lower alkoxyl, a nitro group,

momsnmoQavom l lo:

.butyltin oxide the mdium to high'boiling' saturated aliphatic hydrocar bons such as hexane, cyclohexane, ous ligroins.

Reference is now made to the following examples which are inserted for the purpose of illustrating the invention in greater detail. It is to be pointed out, however, that different modifications in practicing the invention will be evident to those skilled in the art without departing from'the scope or spirit of the said invention.

Example 1.-Dibutyltin bis-(2,4-dinitro-6-t-butylphenolate) Example 2.-Dibutyltin bis-(2-nitro-4-methyl-phenolate) Powdered di-n-butyltin oxide, 12.5 gr. (0.05 mole), and 15.3 gr. of 4-methyl-2-nitro-phenol (0.1 mole) were dispersed in 120 cc. of benzene. After 2 hrs. of reflux 0.7 cc. of -1 had been collected in a Dean-Stark trap, and all dibutyltin oxide had reacted, as indicated by the clear solution. Benzene was removed by distillation, and a light yellow, crystalline material was obtained as residue in quantitative yield (27 gr); M.P. 46 C. The elemental analysis confirmed the proposed structure.

Example 3.--Dii-butyltin bis-(2,6-dibromo-4-nitrophenol) heptane, and the vari- T-his compound was obtained in quantitative yield by refluxing one mole of diisobutyltin oxide with two moles of 2,6-dibromo-4-nitrophenol for 2 hrs. in toluene. The reaction product is a yellow, undistillable oil.

Example 4.-Dibutyltin bis-(2,4-dinitro-6-sec-butylphenolate) A 1000 cc. reaction flask, equipped with a stirrer, a condenser and a Dean-Stark trap was charged with 24 grams (0.1 mole) of 2,4-dinitro-6-sec-buty1 phenolate, 15.2 grams (0.05 mole) dibutyltin dichloride, 8.8 grams of sodium bicarbonate, and =125' cc:

. aogssa of toluenelThe-rnixture was agitated and brought to reflux. After a period of 5 hours, 0.8 cc. of Water had collected in the Dean-Stark trap. The reaction mixture was allowed to cool to room temperature and the benzene solvent was removed by distillation. The reaction product was obtained in quantitative yield (71.0 grams). It .was a red, viscous, undistillable oil.

The dialkyltin bis-ortho-substituted nitrophenolates of the invention have been found to exhibit a variety of new and useful properties and aremoreover not plagued by the hydrolytic or moisture instabilitycharacteristic-of the hitherto'known dialkyltin bis-phenolates. It has,'for instance, been ascertained that the compounds of the invenr tion are effective as herbicides, fungicides 'and'insecticides. In this connection, reference is made to ,Example 1 which when employed at a concentration of pounds/80"gal./

, acre gave complete control of such noxious vegetative growths as crabgrass, annual-bluegrass, water grass, wild oat, pigweed and Indian Mustard. Post-emergence application of the same compound at a rate of 2 lbs./ acre resulted in death or complete eradication ofFoxtail and Mustard after twenty-one'days. Other types of pesticidal organisms which have been found to be susceptible to the compounds of the invention include the common house fly, Musca domestica, and the American cockroach, Periplaneta americana. The compounds are unusually effective against various parasitic protozoa such as poultry coccidia to include Eirrleria acervulina, Eimeria tenella, and Eimeria necatrix. The compounds are particularly effective against Eimria necatrix. For example the compound of Example 4 is found to completely control Eimeria necatrix at a concentration of 250 parts per million. By using the compounds of the invention in relatively dilute concentrations, they were found to be effective in controlling rust and mildew without injuring the host plants.

1 claim: I

1. Dibutyltin bis-(2,4-dinitro-6-t-butyl-phenolate).

2. Dibutyltin bis-(2,4-dinitro-6-sec-butyl-phenolate).

References Cited FORETGN PATENTS 797,073 6/1958 Great Britain.

TOBIAS E. LEVOW, Primary Examiner. W. F. W. BELLAMY, Assistant Examiner. 

